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Good to Know: Cheapest and Fastest SJO - MDW Flights
Useful information for finding best airline tickets from Juan Santamaria International to Chicago Midway International on your next trip.
Cheapest Round Trip Flight
$444
Southwest Airlines
• 1 stop
• 12h 25m
Dec 23 – Dec 27
The cheapest round trip flight from San Jose to Chicago (SJO-MDW-SJO) is currently $444
Fastest Flight
12h 25m
The fastest nonstop flight from San Jose to Chicago (SJO-MDW) takes 12h 25m
Top Airlines Flying from San Jose to Chicago
Latest Flight Deals from San Jose (SJO) to Chicago (MDW)
Compare and book low fare round-trip air tickets from San Jose to Chicago. Ideal for travelers with confirmed return itineraries.
Dec 23 - Dec 27, Economy
San Jose → Chicago
12h 25m
2:10 PM - 9:55 PM • 1 stop
San Jose → Chicago
27h 20m
8:35 PM - 1:15 PM • 1 stop
Southwest Airlines
Dec 23 - Dec 27, Economy
San Jose → Chicago
28h 50m
3:25 PM - 8:55 AM • 2 stops
San Jose → Chicago
12h 30m
5:25 AM - 1:15 PM • 1 stop
Southwest Airlines
Dec 23 - Dec 27, Economy
San Jose → Chicago
27h 35m
2:10 PM - 7:05 AM • 2 stops
San Jose → Chicago
12h 30m
5:25 AM - 1:15 PM • 1 stop
Southwest Airlines
Dec 23 - Dec 27, Economy
San Jose → Chicago
12h 30m
3:25 PM - 11:15 PM • 1 stop
San Jose → Chicago
29h 10m
8:35 PM - 2:25 PM • 2 stops
Southwest Airlines
Dec 23 - Dec 27, Economy
San Jose → Chicago
28h 25m
2:10 PM - 7:15 AM • 2 stops
San Jose → Chicago
12h 30m
5:25 AM - 1:15 PM • 1 stop
Southwest Airlines
FAQs on San Jose to Chicago Flights
What are the airports in San Jose?
SJO
What’s the most popular airline flying from SJO to MDW?
The most popular airline flying from San Jose to Chicago are
Can I fly from SJO to MDW non-stop?
NO
Which airlines fly nonstop between San Jose and Chicago?
The non-stop flights between San Jose and Chicago are .
What’s the earliest departure time from SJO to MDW Airport?
The earliest flight leaves SJO at 2:10 pm and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Jose to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from SJO to MDW?
Read the fare rules of the San Jose to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from San Jose and Chicago?
operate flights between San Jose and Chicago
How long does a flight from San Jose to Chicago take?
It takes approximately 5 hour to fly non-stop from SJO to MDW, which is 2199.5 miles by air.
Which airlines provide the cheapest flights from San Jose (SJO) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SJO were found on WN : USD 448
Do I need a passport to fly between SJO and MDW?
Yes
What’s the latest departure time from SJO to MDW ?
The last flight leaves SJO at 3:25 pm
San Jose (SJO) to Chicago (MDW): Airport Information
| Origin Airport | Juan Santamaria International , San Jose, CR |
| Destination Airport | Chicago Midway International , Chicago, US |
| Distance | 2200 miles |
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